Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination |
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| Authors: | Naoko Nishina |
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| Institution: | Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan |
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| Abstract: | A wide range of alcohols 2 react with various allenes 1 in the presence of ClAuPPh3/AgOTf catalyst at ambient temperature without solvent to produce allylic ethers 3. Contrary to the hydroamination, which proceeds through high chiral-face selectivity for chiral allenes to give the corresponding chiral allylic amines, transfer of chirality is not observed in the hydroalkoxylation, suggesting that the mechanism of the gold-catalyzed hydroalkoxylation is different from that of hydroamination. |
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| Keywords: | Alcohol Allene Chirality transfer Gold catalysis Hydroalkoxylation Allylic ether Silver triflate Gold chloride |
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